Synthesis, structural characterization and in vitro cytotoxicity and anti-bacterial activity of some copper(I) complexes with N,N′-disubstituted thioureas

Rauf, M. Khawar; Imtiaz‐ud‐Din,; Badshah, Amin; Gielen, Marcel; Ebihara, Masahiro; Vos, Dick de; Ahmed, Safeer

doi:10.1016/j.jinorgbio.2009.05.014

Cited by 126 publications

(64 citation statements)

References 39 publications

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“…Chelating thiourea ligands containing N, S and O donor atoms show broad biological activity and the existence of metal ions bonded to biologically active compounds may enhance their activities, and it was shown that the mode of binding of platinum to DNA is affected by the substituent nature on the acyl thiourea [4]. Acyl thiourea derivatives have been increasingly important with a wide diversity of applications in heterocyclic chemistry, metal complexes, molecular electronics and exhibit an array of biological activities [5][6][7][8][9]. Some of them are employed as fungicidal, antiviral, antimicrobial [10], parasiticidal [11], antitumoral [12] and pesticidal agent [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

On the cytotoxic activity of Pd(II) complexes of N,N-disubstituted-N′-acyl thioureas

Plutı́n

Mocelo

Alvarez

et al. 2014

Journal of Inorganic Biochemistry

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Section: Introductionmentioning

confidence: 99%

On the cytotoxic activity of Pd(II) complexes of N,N-disubstituted-N′-acyl thioureas

Plutı́n

Mocelo

Alvarez

et al. 2014

Journal of Inorganic Biochemistry

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“…The higher resonance of NH peaks in d-f at 10.84-10.53 ppm and 10.18-10.01 ppm was due to downfield effect resulting from the formation of intramolecular hydrogen bond between the hydrogen atom from thiourea moieties with oxygen atom from the carboxylic acid group [5].…”

Section: Chemistrymentioning

confidence: 97%

“…Several studies reported on monosubstituted thiourea which consists of one thiourea moiety either as a ligand bearing aromatic, halogen, or alkyl substituents [4] or as a complex compound coordinated with heavy metal center [5]. Multisubstituted thioureas have gained more interest among researchers due to the increase of their pharmaceutical properties.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties

Ngaini

Zulkiplee

Halim

2017

Journal of Chemistry

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In this study, hexasubstituted thiourea was carried out via reaction of isothiocyanato cyclophosphazene intermediates with a series of aromatics amines and amino acids in a one-pot reaction system. The reaction was not as straightforward as typical thiourea synthesis. Six unexpected thiourea derivatives a-f were formed in the presence of cyclotriphosphazene moieties in good yields (53-82%). The structures of a-f were characterized by elemental analysis and FTIR, 1 H, 13 C, and 31 P NMR spectroscopies. The occurrence of reverse thioureas formation in a one-pot reaction system is discussed. The possible binding interaction of the synthesised thiourea a-b in comparison to the predicted phenyl thiourea a-b and the targeted a with enzyme enoyl ACP reductase (FabI) is also discussed. Molecular docking of the targeted hexasubstituted thiourea a is able to give higher binding affinity of −7.5 kcal/mol compared to a-b (−5.9 kcal/mol and −6.3 kcal/mol) and thiourea a-b (−4.5 kcal/mol and −4.7 Kcal/mol).

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“…Interest in the title compound arises from promising cytotoxicity profiles exhibited by palladium(II) (Selvakumaran et al, 2011) and copper(I) (Rauf et al, 2009) . The N1-C2-C3-O1 torsion of 66.9 (2) places the hydroxy-O1 atom in close proximity to the amide enabling the formation of an intramolecular N2-HÁ Á ÁO1 hydrogen bond, Table 1.…”

Section: Structure Descriptionmentioning

confidence: 99%

3-(2-Hydroxyethyl)-3-methyl-1-(4-methylbenzoyl)thiourea

2016

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The title thiourea derivative, C 12 H 16 N 2 O 2 S, has a twisted conformation with the dihedral angle between the NC( S)N and O CC 6 planes being 35.45 (5) . The observed conformation allows for an intramolecular N-HÁ Á ÁO hydrogen bond. In the molecular packing, supramolecular aggregation is based on hydroxy-O-HÁ Á ÁO(carbonyl) hydrogen bonding and leads to supramolecular helical chains along the a axis; chains are reinforced by N-methylene-C-HÁ Á ÁS and N-methyl-C-HÁ Á Á(arene) interactions. Supramolecular layers in the ab plane are formed as a result of tolyl-methyl-C-HÁ Á Á(arene) interactions. Structure descriptionInterest in the title compound arises from promising cytotoxicity profiles exhibited by palladium(II) (Selvakumaran et al., 2011) . The N1-C2-C3-O1 torsion of 66.9 (2) places the hydroxy-O1 atom in close proximity to the amide enabling the formation of an intramolecular N2-HÁ Á ÁO1 hydrogen bond, Table 1.In the crystal, supramolecular helical chains are formed along the a axis and are sustained by a combination of hydroxy-O-HÁ Á ÁO(carbonyl) hydrogen bonding, and Nmethylene-C-HÁ Á ÁS and N-methyl-C-HÁ Á Á(arene) interactions. Connections between the chains are of the type tolyl-methyl-C-HÁ Á Á(arene) and occur along the b axis

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Synthesis, structural characterization and in vitro cytotoxicity and anti-bacterial activity of some copper(I) complexes with N,N′-disubstituted thioureas

Cited by 126 publications

References 39 publications

On the cytotoxic activity of Pd(II) complexes of N,N-disubstituted-N′-acyl thioureas

On the cytotoxic activity of Pd(II) complexes of N,N-disubstituted-N′-acyl thioureas

One-Pot Multicomponent Synthesis of Thiourea Derivatives in Cyclotriphosphazenes Moieties

3-(2-Hydroxyethyl)-3-methyl-1-(4-methylbenzoyl)thiourea

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